But nay saying commenters call the video speaker a huckster, and others challenge the concept that it’s even possible to do what you love (and get paid for it, and still love it).

As somebody who is technically doing what I love, I find this fascinating. I travel full-time in a financially sustainable manner, paid for by a writing career that is fulfilling. I do what I love (ie: travel and writing), and I make enough money at it to get by.

But even my situation isn’t as black & white as that. In further examining the intricacies of love and money, here are some concepts that further deepen the debate.

Doing what you love isn’t always a bowl of cherries

Just because you do what you love doesn’t mean you love everything about what you do. The speaker suggested that there are certain aspects of his job that he full-on hates. I concur: there are times when I want to stab myself in the eye if I have to spend one more hour at my computer when the weather is nice and an exotic unknown destination beckons from just outside my window.

But without my writing, there wouldn’t be an exotic destination outside my window at all; I’d still be cooped up in an office somewhere working at a career I was equally marvelous and miserable at.

I also make a number of frugal lifestyle choices in order to get by with the money I make on the road. For some people it wouldn’t be ideal, and for others it would be unacceptable; it is a very personal choice.

But for me, the benefits of my writing career (and the accompanying travel lifestyle) far outweigh the costs. But there is still a cost. No dream is THAT dreamy.

Early career choices (and life partners for that matter) are like shots in the dark

Choosing any career is like choosing a life partner. How do we know once we have just escaped the throes of adolescence what career will make us happy every day for the rest of our life?

Similarly, how do we know (at any age) if we will be happy waking up next to our partner every morning for the rest of our life — happy enough to get married?

Guess what? Most people don’t know.

And because we are required to decide on our post-secondary education (and the range of careers it lends us) at such a young age (arguably before we really know ourselves), many of us end up studying for careers we ultimately won’t be happy in.

But what do we do after we have gotten our degree and are now working our way up a career ladder in order to:

What do we do when faced with inevitable bills and financial goals? That’s right. Put on the blinders, keep our head down, and work. We may not be thrilled with our job, but we justify it as a means to an end (the various "ends" being listed above). We keep company with other people who also don’t particularly like what they do, and — since most people are in this boat — commiserating becomes natural.

This is how being somewhat unhappy with a career becomes an acceptable way of life. It is much easier and safer to go with what we know (despite the fact that it may not be entirely what we want) than to uproot our routine or balance to explore a new avenue.

Other people, however, see life as too long to get stuck doing something (or being with someone) that is not fulfilling. These people forgive themselves for not making the right life-enduring decision, and search for ways to improve. Ways could include changing careers, starting businesses on the side, taking up new hobbies, and finding new partners.

The bigger these people dream, the bigger the changes they make are. And who are the big dreamers? I believe that some of the world’s biggest dreamers are also some of the most entrepreneurial.

Entrepreneurs vs. Employees

I am wondering if the core root of the matter (and where each of us fits in the spectrum) boils down to how entrepreneurial — or not — we are.

Entrepreneurs don’t mind working hard for what they want, and they look for creative ways to get there. If strictly doing what they love has obscure career prospects, they find a different spin on it that makes it more lucrative.

It is likely that only the entrepreneurial souls understood the vision the speaker had when he spoke of working a full-time job, then coming home and working another seven hours on his business for the first five years. Most of us would crunch the numbers and say he’s crazy. But he had a vision for a niche idea that took five years to develop, and develop it he did.

Although that sort of lifestyle may sound unbalanced (and it is), if we are doing what we love, we don’t tend to mind doing it so much. When we do what we love, we don’t mind the sacrifices and compromises we may have to make. Why? Because if we are really doing what we love, we simply wouldn’t have it any other way.

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Great article! Life is full of shades of gray (or should I say tints of the rainbow?). Any worthwhile goal, like living your dream job or dream life, has to be pursued with patience and fortitude. Success rarely drops into our laps, and even when it comes, it comes with some compromises.

The same analogy can be made with successful investing. It takes some homework, some time, and maybe some sacrifices. Thanks for the interesting thoughts Nora.

"When we do what we love, we don’t mind the sacrifices and compromises we may have to make."

I think the implicit assumption is that there are not other lives impacted by our choices. Are you saying that for you writing is the only dream you have that matters? Do you have any dreams/goal around relationships in your life.

I could work very long hours pursuing my every dream while ignoring my kids, wife and other relationships. When I finally do achieve my goal/dream these people may have moved on, having given up on a the relationship I was too busy to nurture.

If you are already married with kids and suddenly decide to purse a life long dream of travel and writing telling your family "see you later" can be devastating to THEIR lives. Is that selfish?

It would seem to me that making "compromises" (breaking existing commitments) in other areas of personal life so that your dream is fulfilled is no better than compromising the dream.

For me it is a constant struggle or balancing act. I love what I do, I hate my industry. I'm building my business, I want my free time. I hate sales people, I am a sales person. I don't want to work 80 hrs per week, I need to make money.

I think a lot of people face these dilemmas, maybe even more so with entrepreneurs. In the end I love what I do and I love the freedom it gives me. Then I constantly search to get the other things I want such as more money and to do more traveling. All in due time?

I've been both many times. I would never go into a full time Business again, I once owned a gas station, and spent more 16 hour days then I cared to, and the feeling of never being able to leave town,etc. I think if you owned a business where it didn't matter if you were open, or not retail, but a service business, where you were the business, not one with reselling of goods.
A Job, when you get 2 weeks vacation, schedualed days off, benefits Your off at 6:00 to put away your work brain, etc. I was relieved to go to a day job after owning my own gas station. I was in heaven.

There is good and bad in everything, and at the end of the day You have to do what is right for you.

I will heartily agree that doing what you love doesn't necessarily mean that you love everything about what you're doing. I'm currently doing exactly what I love, after having worked 7 years in finance, excelling at it but secretly yearning for the time where I would be self-employed. Yet, I didn't want to be attached to a geographical location, and I didn't want to have to work 16 hour days forever.

Right now, I'm by no means making millions, but I do think I have found a happy medium. Some days I can afford to take off, some others I have to sit my ass down in front of a computer and work pretty much around the clock. But overall I'm very happy being self-employed and I'm hoping never having to be an employee another day of my life.

There is a price to pay for this, though. I build and maintain websites for a living, and I keep drawing blank stares whenever someone asks me "What do you do for a living" and I tell them. Most of the time, they think I'm an unemployed loser who just doesn't want to say he's not working. The funny thing is that I probably out-earn most of these people, but not having a steady job makes you very cautious about how you spend your money. So I have no bling to show, lol...

Finally, my journey was made easier by the fact that I didn't have to think about a girlfriend nor kids, and could afford to focus on my dream. Not everyone has this luxury. In the end, it's all about choices and specific life circumstances...

Life can really turn out much different than originally planned and that is not a bad thing. The unexpected experiences may even be beneficial once a person reaches different points along the way where they can stop and access things. Ultimately the more time a person spends enjoying whatever they do the more successful they are.

I dunno, I have to say that I'd love your job, Nora. ;) So far, I'm working on how to track down writing assignments on the subject that I prefer to write about while improving my writing and building my own site.

I'm still puzzled about how to make a living working with my passion and love -- cars. I know I'll figure it out eventually... It's just taking longer than I wish it would!

I'm looking forward to an aha! sort of moment, or just an idea that's not as physical of work (So that I too could travel or take time off as I please), but I do have one tiny idea that I keep coming back to... A sign, perhaps?

The best part of looking for my break-through (to me) idea is that I have a loving husband who'll support all those crazy ideas to live life on my own terms, sometimes because he cannot live that way yet. (Military.)

There are always sacrifices to be made before, during and after a chosen action. The picture that some people have about their life - personal, professional, spiritual - is often unrealistic and causes unhappiness. You make a good point that "doing what you love to make a living" isn't always fun or rewarding. Everyone has to decide for themselves what is enough for them.

If you are already married with kids and suddenly decide to purse a life long dream of travel and writing telling your family "see you later" can be devastating to THEIR lives. Is that selfish?

You make a great observation about relationships, and honoring commitments you have made. Once again, I don't believe that one has to come without the other. If you love your wife and kids, then your lives will evolve together, as you - individually and collectively - search out what you love. (PS - I know entire families who travel).

Just in case you were wondering, I didn't leave a husband and kids behind; I don't have kids, and the hubby and I decided to travel together!

I could work very long hours pursuing my every dream while ignoring my kids, wife and other relationships. When I finally do achieve my goal/dream these people may have moved on, having given up on a the relationship I was too busy to nurture.

Good one. I don't have an answer for that. I don't know if the speaker had a wife and kids who stood in the sidelines while he worked so hard for those five years. I know many people who have been on both sides of that dilemna, and it is a very difficult one to navigate. This is where communication and (acceptable) compromises are necessary.

One of the buried themes in this article (I believe) is that live is an evolution. I wonder if it's when we get stuck in a life of mediocrity (in our eyes) that things start to go downhill.

It's kind of like the stories of two frogs in pots. The first frog was chucked into a pot of hot water. He immediately jumped out to safety, as you do. The second frog, however, was put into a pot of luke warm water which was heated slowly. It didn't perceive the gradual change in temperature until the water was too hot for the frog to save itself.

@CanadianFreeStuff - You say you are happier now with a "regular" job than you were owning a business. You're not alone! Other commenters have touched on this too; this goes to show just how many "tints of rainbow" (as @SilverPurseGal says) there are! Good for you for having the courage to make a big career change in your life too; keep chasing what you love, whatever that may be for you right now!